As universities internationalize and attract students from multiple transnational locations, more innovative curriculum design is developed that enables students and staff to communicate and act globally. When developing a global perspective in universities, creating the capacity to deliver programs in diverse international arenas is essential. Academic teaching staff strive to design collaborative learning experiences that enable students to engage in activities that deepen their cross-cultural knowledge, a capability that is required for future employment. However, the reality of designing and implementing learning activities in a transnational education program with culturally unfamiliar contexts that engages students is challenging. This chapter will use the lessons learnt from a case study of a transnational education project designed as part of a university global program. This project involved undergraduate students across an umbrella course (Global Learning by Design which incorporated international business and strategic management) within the management discipline, offered in Australia, Vietnam, and Singapore. It presents the key challenges for universities in implementing learning experiences that develop cross-cultural competencies. These challenges include resource management and allocation; pedagogical challenges in learning and communication; and management of normative values and students’ expectations, particularly in group tasks. The course aimed to empower students through the development of skills in cross-cultural management to contribute to decisions within diverse political, economic, environmental, and social contexts; and to work collaboratively and pursue continuous personal development related to their future as management professionals. The case study reflects the complexity of business and team engagement on multiple dimensions and provides opportunities for analysis and reflection at a deeper learning level, and a reduction of cross-cultural bias. The authors suggest that to address these challenges universities will need to consider issues of power and inequality inherent in teaching partnerships, and undergo a mindset change in order to develop global perspectives.